Asymmetric Synthesis of 4,8-Dihydroxyisochroman-1-one Polyketide Metabolites Using Chiral Hypervalent Iodine(III)

2012 ◽  
Vol 14 (5) ◽  
pp. 1294-1297 ◽  
Author(s):  
Morifumi Fujita ◽  
Kazuhiro Mori ◽  
Mio Shimogaki ◽  
Takashi Sugimura
Keyword(s):  
Asymmetric Synthesis ◽  
Hypervalent Iodine

New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

1998 ◽  
Vol 63 (22) ◽  
pp. 7674-7679 ◽  
Author(s):  
Urs H. Hirt ◽  
Bernhard Spingler ◽  
Thomas Wirth
Keyword(s):  
Asymmetric Synthesis ◽  
Hypervalent Iodine ◽  
Iodine Compounds

Oxidative Cyclization of Naphtholic Sulfonamides Mediated by a Chiral Hypervalent Iodine Reagent: Asymmetric Synthesis versus Resolution

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1222-1227 ◽  
Author(s):  
Nikita Jain ◽  
Jason E. Hein ◽  
Marco A. Ciufolini
Keyword(s):  
Asymmetric Synthesis ◽  
Trifluoroacetic Acid ◽  
Oxidative Cyclization ◽  
High Yield ◽  
Hypervalent Iodine ◽  
Aryl Iodide ◽  
Seed Crystals ◽  
Enantioselective Reaction ◽  
Low Efficiency

A chiral aryl iodide promotes the enantioselective oxidative cyclization of 1-naphtholic sulfonamides, albeit in moderate ee and low yield. The products tend to crystallize as conglomerates. Recrystallization thus increases their ee to > 99% ee. This highly enantioenriched material provides seed crystals for the resolution of the racemate (prepared in high yield by oxidative cyclization with (diacetoxyiodo)benzene in trifluoroacetic acid) by coupled preferential crystallization. This enables the production of significant quantities of highly enantioenriched products, despite the low efficiency of the enantioselective reaction.

scholarly journals A survey of chiral hypervalent iodine reagents in asymmetric synthesis

2018 ◽  
Vol 14 ◽  
pp. 1244-1262 ◽  
Author(s):  
Soumen Ghosh ◽  
Suman Pradhan ◽  
Indranil Chatterjee
Keyword(s):  
Transition Metals ◽  
Asymmetric Synthesis ◽  
Environmentally Friendly ◽  
Hypervalent Iodine ◽  
Asymmetric Transformations ◽  
Iodine Chemistry

The recent years have witnessed a remarkable growth in the area of chiral hypervalent iodine chemistry. These environmentally friendly, mild and economic reagents have been used in catalytic or stoichiometric amounts as an alternative to transition metals for delivering enantioenriched molecules. Varieties of different chiral reagents and their use for demanding asymmetric transformations have been documented over the last 25 years. This review highlights the contribution of different chiral hypervalent iodine reagents in diverse asymmetric conversions.

ChemInform Abstract: New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis.

ChemInform ◽  
2010 ◽  
Vol 30 (12) ◽  
pp. no-no
Author(s):  
Urs H. Hirt ◽  
Bernhard Spingler ◽  
Thomas Wirth
Keyword(s):  
Asymmetric Synthesis ◽  
Hypervalent Iodine ◽  
Iodine Compounds
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